Novel and efficient synthesis of fused spiro piperidone-cyclopropanes from cascade reaction of 1-acylcyclopropanecarboxamides and polarized olefin

2021 ◽  
Author(s):  
Xiao Dan Han ◽  
Gao Liang Peng ◽  
Hui Bin Wang ◽  
lei wu ◽  
Jian Ping Fu ◽  
...  
Keyword(s):  
Cascade Reaction ◽  
Single Step ◽  
Efficient Synthesis ◽  
One Pot ◽  
The One ◽  
Cyclopropane Derivatives

We report here that a series of O-bridged ring fused spiro piperidone-cyclopropane derivatives 3 can be constructed in a single step by the one-pot reaction of 1-acylcyclopropanecarboxamides 1 with polarized...

scholarly journals 2-Ketoglutarate-Generated In Vitro Enzymatic Biosystem Facilitates Fe(II)/2-Ketoglutarate-Dependent Dioxygenase-Mediated C–H Bond Oxidation for (2s,3r,4s)-4-Hydroxyisoleucine Synthesis

2020 ◽  
Vol 21 (15) ◽  
pp. 5347
Author(s):  
Xiao-Ran Jing ◽  
Huan Liu ◽  
Yao Nie ◽  
Yan Xu
Keyword(s):  
Amino Acids ◽  
Raw Materials ◽  
Cascade Reaction ◽  
Single Step ◽  
One Pot ◽  
Bond Functionalization ◽  
Hydroxy Amino ◽  
Enzymatic Systems ◽  
The One

Fe(II)/2-ketoglutarate-dependent dioxygenase (Fe(II)/2-KG DO)-mediated hydroxylation is a critical type of C–H bond functionalization for synthesizing hydroxy amino acids used as pharmaceutical raw materials and precursors. However, DO activity requires 2-ketoglutarate (2-KG), lack of which reduces the efficiency of Fe(II)/2-KG DO-mediated hydroxylation. Here, we conducted multi-enzymatic syntheses of hydroxy amino acids. Using (2s,3r,4s)-4-hydroxyisoleucine (4-HIL) as a model product, we coupled regio- and stereo-selective hydroxylation of l-Ile by the dioxygenase IDO with 2-KG generation from readily available l-Glu by l-glutamate oxidase (LGOX) and catalase (CAT). In the one-pot system, H2O2 significantly inhibited IDO activity and elevated Fe2+ concentrations of severely repressed LGOX. A sequential cascade reaction was preferable to a single-step process as CAT in the former system hydrolyzed H2O2. We obtained 465 mM 4-HIL at 93% yield in the two-step system. Moreover, this process facilitated C–H hydroxylation of several hydrophobic aliphatic amino acids to produce hydroxy amino acids, and C–H sulfoxidation of sulfur-containing l-amino acids to yield l-amino acid sulfoxides. Thus, we constructed an efficient cascade reaction to produce 4-HIL by providing prerequisite 2-KG from cheap and plentiful l-Glu and developed a strategy for creating enzymatic systems catalyzing 2-KG-dependent reactions in sustainable bioprocesses that synthesize other functional compounds.

scholarly journals Tandem four-component reaction for efficient synthesis of dihydrothiophene with substituted amino acid ethyl esters

RSC Advances ◽  
2018 ◽  
Vol 8 (40) ◽  
pp. 22498-22505 ◽  
Author(s):  
Jing Sun ◽  
Yu Zhang ◽  
Chao-Guo Yan
Keyword(s):  
Amino Acid ◽  
Aromatic Aldehydes ◽  
Ethyl Esters ◽  
Efficient Synthesis ◽  
One Pot ◽  
The One

The one-pot four-component reaction of aromatic aldehydes, malononitrile, 1,3-thiazolidinedione and ethyl glycinate hydrochloride in ethanol in the presence of triethylamine afforded trans-dihydrothiophene.

New efficient synthesis of benzofuro[2,3-b]pyrroles utilizing a reactive nitrilium trapping approach by an acid-promoted cascade addition/cyclization sequence

2020 ◽  
Vol 44 (9) ◽  
pp. 3632-3636
Author(s):  
Sandip Gangadhar Balwe ◽  
Yeon Tae Jeong
Keyword(s):  
Cascade Reaction ◽  
Efficient Synthesis ◽  
One Pot ◽  
Highly Efficient

The first p-TSA·H2O-catalyzed highly efficient one-pot cascade reaction for the synthesis of novel fused tricyclic benzofuro[2,3-b]pyrroles has been discovered.

Visible-Light Photoredox-Catalyzed Cascade Reaction for the Synthesis of Pyrrolo[2,1-a]isoquinoline-Substituted Phosphonates

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 522-529 ◽  
Author(s):  
Deqing Shi ◽  
Lingna Wang ◽  
Tiancong Ma ◽  
Mingming Qiao ◽  
Qiangxian Wu ◽  
...  
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Cascade Reaction ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Oxidative Aromatization ◽  
Activated Olefins ◽  
Catalyzed Oxidation

A visible-light photoredox-catalyzed oxidation/[3+2] cycloaddition/oxidative aromatization cascade reaction of [(3,4-dihydroisoquinolin-2(1H)-yl)methyl]phosphonates and activated olefins or alkynes for the efficient synthesis of potentially biological active pyrrolo[2,1-a]isoquinoline-substituted phosphonates was developed. This transformation features mild reaction conditions (i.e., visible light irradiation, room temperature), molecular oxygen (O2) as a green oxidant, simple ‘one-pot’ operation.

Palladium(II)-Catalyzed Three-Component Tandem Cyclization Reaction for the One-Pot Assembly of 4-Arylquinazolines

Synthesis ◽  
2020 ◽  
Author(s):  
Guolin Zhang ◽  
Yongping Yu ◽  
Zijuan Wang ◽  
Wenteng Chen ◽  
Chang He
Keyword(s):  
Bond Formation ◽  
Cascade Reaction ◽  
Cyclization Reaction ◽  
One Pot ◽  
Tandem Cyclization ◽  
The One

AbstractA one-pot method for joining three separate components leading to an assortment of 4-arylquinazolines (27 examples) in good to excellent yields is described. The method consists of a palladium(II)-catalyzed­ cascade reaction involving C(sp)–C(sp2) coupling followed by intramolecular C–N bond formation. The reaction was readily scaled up to gram quantity and successfully applied to the synthesis of a translocator­ protein (TSPO) ligand.

Single-step formulation of levodopa-based nanotheranostics – strategy for ultra-sensitive high longitudinal relaxivity MRI guided switchable therapeutics

2020 ◽  
Vol 8 (6) ◽  
pp. 1615-1621
Author(s):  
Dan Tian ◽  
Hongxia Xu ◽  
Bing Xiao ◽  
Xiaoxuan Zhou ◽  
Xiangrui Liu ◽  
...  
Keyword(s):  
Photothermal Therapy ◽  
Single Step ◽  
Tumor Ablation ◽  
One Pot ◽  
Mri Contrast ◽  
Longitudinal Relaxivity ◽  
Mri Guided ◽  
The One ◽  
Complete Tumor

The one-pot synthesized nanotheranostic agent T-SWITCH showed high MRI contrast efficiency (r1 = 61.94 mM−1 s−1) and complete tumor ablation after photothermal therapy.

scholarly journals Sustainable synthesis of 3-substituted phthalides via a catalytic one-pot cascade strategy from 2-formylbenzoic acid with β-keto acids in glycerol

2017 ◽  
Vol 13 ◽  
pp. 1425-1429 ◽  
Author(s):  
Lina Jia ◽  
Fuzhong Han
Keyword(s):  
Natural Products ◽  
Cascade Reaction ◽  
Catalytic Process ◽  
Efficient Synthesis ◽  
One Pot ◽  
Keto Acids ◽  
Synthesis Strategy ◽  
Therapeutic Activities

Background: Phthalides are privileged constituents of numerous pharmaceuticals, natural products and agrochemicals and exhibit several biological and therapeutic activities. Therefore, the development of new, facile, and sustainable strategies for the construction of these moieties is highly desired. Results: A broad substrate scope for β-keto acids was found to be strongly compatible with this catalytic process, affording a wide variety of 3-substituted phthalides in good to excellent yields. Conclusion: A concise and efficient synthesis strategy of 3-substituted phthalides from 2-formylbenzoic acid and β-keto acids via a catalytic one-pot cascade reaction in glycerol has been accomplished.

scholarly journals An Efficient Synthesis of 1,8-Dioxo-Octahydroxanthenes Derivatives Using Heterogeneous Ce-ZSM-11 Zeolite Catalyst

2018 ◽  
Vol 13 (3) ◽  
pp. 436 ◽  
Author(s):  
Rameshwar R. Magar ◽  
Ganesh T. Pawar ◽  
Sachin P. Gadekar ◽  
Machhindra Karbhari Lande
Keyword(s):  
Zeolite Catalyst ◽  
Bet Surface Area ◽  
High Yield ◽  
Efficient Synthesis ◽  
X Ray Diffraction ◽  
One Pot ◽  
Efficient Catalyst ◽  
Temperature Programmed ◽  
The One ◽  
Work Up

The Ce-ZSM-11 zeolite has been used as an efficient catalyst for the one pot synthesis of 1,8-dioxo-octahydroxanthene derivatives from aromatic aldehyde and 5,5-dimethyl-cyclohexane-1,3-dione under reflux condition. The catalyst was characterized by Powder X-ray diffraction (XRD), Scanning Electron Microscopy (SEM), Energy Dispersive Spectroscopy (EDS), Fourier Transform Infrared Spectroscopy (FTIR), Brunauer-Emmer-Teller (BET) surface area analysis, and Temperature Programmed Desorption (TPD) techniques. This method provides several advantageous such as use of inexpensive catalyst, simple work-up procedure, high yield of desired product and reusability of catalyst. Copyright © 2018 BCREC Group. All rights reservedReceived: 5th January 2018; Revised: 25th May 2018; Accepted: 27th May 2018How to Cite: Magar, R.R., Pawar, G.T., Gadekar, S.P., Lande, M.K. (2018). An Efficient Synthesis of  1,8-Dioxo-Octahydroxanthenes Derivatives Using Heterogeneous Ce-ZSM-11 Zeolite Catalyst. Bulletin of Chemical Reaction Engineering & Catalysis, 13 (3): 436-446 (doi:10.9767/bcrec.13.3.2062.436-446)Permalink/DOI: https://doi.org/10.9767/bcrec.13.3.2062.436-446 

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